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Your Guide to Cinco de Mayo in Chicago

Last Updated July 21, 2017

One of the many perks of being in Chicago is knowing that great food is never far away. You can find tasty treats from almost any type of cuisine on the planet, but Chicago truly has a plethora of excellent Mexican Restaurants. Seriously, is there anyone who doesn’t love Mexican food? It’s absolutamente delicioso (that’s “absolutely delicious” for those who don’t know Spanish). For those who want an excuse to sit on a patio, drink some margaritas, and chow down on tacos; we’ve got ideas for you. Below are some of our picks for you to go eat, drink and be merry this Cinco de Mayo in Chicago(click restaurant names for more info).

EAT

This holiday trumps any Taco Tuesday you’ve ever celebrated. Do it right, stop by one of the places below.



Big Star

There’s big news in Wicker Park; Big Star and Dove’s Luncheonette have paired up to offer breakfast tacos on the weekends and what better day to debut this that on Cinco de Mayo? Not only are they debuting these tacos, but they’re offering them for free (9-11am, limit one per person)! Let’s be honest; there’s going to be a line, but it’s for FREE Big Star Breakfast Tacos, there is no downside.

This is a prime patio day! ☀️🌮

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XOCO (Chicago or Wicker Park)
You could have the perfect Cinco de Mayo meal at Rick Bayless’ inviting neighborhood Mexican Bistro and Bar. Start with choose-your-topping guacamole, grab a torta, pair it with a hand-shaken margarita and then pull it all together with a stack of churros. At XOCO their freshly-fried, melt in your mouth churros are paired with a chocolate shot. Xoco’s chocolate is unlike any other in the city, because according to their website they are “the only restaurant in Chicago with its own bean-to-cup chocolate program. Huge sacks of cacao beans arrive at our door from Tabasco”. This picture shows a tower of churros, you should need no more information to be convinced.

We're gonna need a bigger chocolate shot…!!! #churrotower

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Taqueria Los Barillitos
Cruise down 25th Street and you’ll find several bustling Mexican options like Taqueria Los Barillitos. Walk in and you’ll find a spit of rotating pork beckons you, and as you order they’ll slice the chile-stained pork directly onto fresh tortillas. They do al pastor right and keep it tender and caramelized.

Antique Taco:
It’s hard to pick a favorite at this cute Wicker Park spot, largely due to the ever-changing menu. A staple for the restaurant which is always available is the mushroom taco (mushrooms supplied by Wisconsin’s River Valley Ranch). The mushrooms are quickly grilled, then served with crunchy escabeche, bright green kale and cooling cilantro crema.

Taco Assembly Line #kitchenlife

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Tallboy Taco
This great taco spot has great Cinco de Mayo specials. Tallboy Taco is offering a taco + Tecate special for $5. Individually, Tecate and Tecate Light will be sold for $3. They’re also putting out $8 Margaritas from 5-7 for happy hour. Between the amazing food, quality service and friendly atmosphere, you’ll have a great Cinco de Mayo here.

Nana
Enjoy a multi-course Mexican dinner at Nana for Cinco de Mayo, with dishes like kingfish ceviche and cochinita pibil. The dinner is four courses with pairings and is $35 per person. Reservations are required and can be made at 312-929-2486.

Bbq tacos at #nana

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Taco Joint
Taco Joint will offer $5 off of all margaritas by the bottle and a $5 beer + tequila shot: with a can of Modelo Especial and a shot of El Jimador blanco tequila.

DRINK

It wouldn’t be a true Cinco de Mayo celebration if margaritas aren’t involved. Stick with the classic or be adventurous with a new flavor.


Antique Taco: House Rosemary Margarita
No surprise that a trendy taco joint also has trendy margaritas. At Antique Taco, the simple margarita (tequila with fresh lime and orange juices) gets spiced up with rosemary simple syrup. Finished with a sprig of rosemary, it’s available both by the pint and quart. Let’s take into consideration that it’s a day of celebration, so you’ll want to go big.

Big Star: Classic Margarita
Big Star makes a solid, classic margarita with Lunazul Blanco, lime and orange curacao. Get some friends, grab a pitcher of margs and order some of the best tacos in town.

Best Intentions: Horchata Margarita
A funky option for those wanting to expand your margarita palate. Best Intentions has a classic Chicago bar feel with the bonus of a fantastic patio. Try the Horchata Margarita, it has the right amount of sweetness and is great for an after work cocktail.

La Ciudad: BYOB
This BYOB option is great for enjoying those that just want to enjoy a 6-pack of Dos Equis or Modelo and some good food. La Ciudad’s affordable menu items are true to Mexico City style, like their quesadillas which are fried and almost like empanadas. Housemade salsas and moles kick their dishes up a notch. More importantly (if they enforce it at all) there’s a minimal corkage fee and the nearby liquor store is Azusa Liquor: 4411 Broadway.

BE MERRY

Here are some options for those who want to enjoy more than just tacos with a few drinks. You know who you are (hint: you probably already have your sombrero ready to go).


Carnivale: Cinco de Mayo Party
Date: Thursday, May 5
Mariachi bands and margaritas will be aplenty at Carnivale’s Cinco de Mayo celebration. There will also be a taco station with $2.50 tacos and a cigar roller, if you like to partake. Drink specials include an $8 classic margarita and $8 El Diablo, the more adventurous option.

 

Frontier, Lottie’s Pub & Pony Inn: Trolley Crawl
Thursday, May 5th

Hop on a trolley between Frontier, Lottie’s Pub and the Pony Inn and enjoy drink specials like $3.50 Dos Equis and tacos. Start at Lottie’s (the trolley crawl headquarters) for a Don Julio brand meet and greet and then head to the Pony Inn, where the MP3 Amigos will be leading the party all night long. Did we mention the trolley’s free and they have giveaways? Trolley starts at 7pm.

Federales/Gaslight: Pub Crawl
Thursday, May 5th – 7 p.m.
Follow a trail of Tacos & Tequila from Gaslight to Schoolyard to Kirkwood!
$25 Tickets and more information available here.

Cinco de Miler
Date: Saturday, May 7, 9:00 a.m.
For those looking for a more active and unique way to celebrate Cinco de Mayo this year, why not run a marathon? A much healthier alternative than back to back margaritas or tequila shots, Cinco de Miler is a 15k & 5k race. Taking place on May 7 this year, Cinco de Miler will help support The 100 Club of Chicago, an organization that helps provide for the families of first responders who lost their lives in the line of duty. A worthy cause that you can salute after the race with a refreshing margarita (you’ll burn the calories off running, it’s fine).

Whiskey and Tequila Fest: Moe’s Cantina & Old Crow
Date: Saturday, May 7, Noon – 4:00 p.m.
What’s better than a Cinco de Mayo party? Well, how about one also celebrates the Kentucky Derby? This year at Moe’s Cantina & Old Crow in River North you can celebrate both at the Whiskey and Tequila Festival. Go and sample over 50 unique whiskeys, bourbons, tequilas and mezcals and participate in the best Derby Hat and Best Sombrero contests. Now the real question is: which hat do you wear?


Don’t like Mexican food? We can’t relate, but here’s a special you might like:

Tuscany Restaurant
Dine at Tuscany on Cinco de Mayo for lunch or dinner and you can purchase $5 pizzas and margaritas. Pizza selections include margherita; speck with gorgonzola, smoked prosciutto and mozzarella; funghi e taleggio with arugula and truffle oil; affumicata with smoked mozzarella, apple bacon, tomatoes, caramelized onion; and others.This is a great option for people who aren’t fond of Mexican food, but still want to feel included.


 

Have you had tacos, margaritas or good times at one of the places mentioned above? Let us know more by commenting below!

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